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Synthesis of a New Class of C 2 ‐Symmetrical Biheteroaryls by Ammonium Cerium(IV) Nitrate Mediated Dimerization of 2‐(Furan‐3‐yl)pyrroles
Author(s) -
Alcaide Benito,
Almendros Pedro,
Carrascosa Rocío,
Torres M. Rosario
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901314
Subject(s) - chemistry , furan , pyrrole , cerium , ammonium nitrate , ammonium , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry
Polyfunctionalized 2‐(furan‐2‐yl)pyrroles and 2‐(furan‐3‐yl)pyrroles derived from 2‐azetidinone‐tethered allenes by two independent cerium(IV)‐mediated single‐electron oxidations provided a (4‐oxopent‐2‐enoyl)pyrrole and 3,3′‐bis(pyrrol‐2‐yl)‐2,2′‐bifurans, respectively. Access to the oxidation precursors was achieved by regiocontrolled cyclization of β‐allenamine intermediates derived from selective β‐lactam nucleus breakage of 2‐azetidinone‐tethered allenols.